Chemistry / Organic Chemistry 9 / Chapter 9 / Problem 9

Organic Chemistry | 9th Edition | ISBN: 9781305080485 | Authors: John E. McMurry

The mercury-catalyzed hydration of alkynes involves the

Chapter 9, Problem 9

(choose chapter or problem)

The mercury-catalyzed hydration of alkynes involves the formation of an organomercury enol intermediate. Draw the electron-pushing mechanism to show how each of the following intermediates is formed.

Equation Transcription:

$C\equiv{}CH$

${H}_{2}O,{H}_{2}S{O}_{4}$

$HgS{O}_{4}$

$H{g}^{+}S{{O}_{4}}^{2-}$

${H}_{3}C-C\equiv{}C-H$

${H}_{2}O,{H}_{2}S{O}_{4}$

$HgS{O}_{4}$

${H}_{3}C$

$H{g}^{+}S{{O}_{4}}^{2-}$

$C\equiv{}C-H$

${H}_{2}O,{H}_{2}S{O}_{4}$

$HgS{O}_{4}$

$H{g}^{+}S{{O}_{4}}^{2-}$

Text Transcription:

C equiv CH

H_2O,H_2SO_4

HgSO_4

Hg^+SO_4^2-

H_3C-C equiv C-H

H_2O,H_2SO_4

HgSO_4

H_3C

Hg^+SO_4^2-

C equiv C-H

H_2O,H_2SO_4

HgSO_4

Hg^+SO_4^2-

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